4,4,5,5-Tetradehydro-11-deoxy-PGE1 analogs

ABSTRACT

This invention comprises certain analogs of the prostaglandins in which there is a triple bond between C-5 and C-6 or C-4 and C-5. Also provided in this invention, are novel chemical processes useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.

The present application is a divisional application of Ser. No. 619,077,filed Oct. 2, 1975, now issued as U.S. Pat. No. 4,013,695, on Mar. 22,1977.

The present invention relates to prostaglandin analogs for which theessential material constituting a disclosure therefor is incorporated byreference here from U.S. Pat. No. 4,013,695, issued Mar. 22, 1977.

I claim:
 1. A prostaglandin analog of the formula ##STR1## wherein g isone, 2, or 3; WHEREIN Y is trans--CH=CH--;wherein M₁ is ##STR2## whereinR₅ is hydrogen or methyl; WHEREIN M IS ONE TO 5, INCLUSIVE; Wherein L₁is ##STR3## wherein R₃ and R₄ are hydrogen, methyl, or fluoro, being thesame or different, with the proviso that one of R₃ and R₄ is fluoro onlywhen the other is hydrogen or fluoro; and wherein R₁ is hydrogen, alkylof one to 12 carbon atoms, inclusive, cycloalkyl of 3 to 10 carbonatoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl,phenyl substituted with one, two, or three chloro or alkyl of one to 3carbon atoms, inclusive, or a pharmacologically acceptable cation.
 2. Acompound according to claim 1, wherein M₁ is ##STR4##
 3. A compoundaccording to claim 1, wherein M₁ is ##STR5##
 4. A compound according toclaim 3, wherein g is
 3. 5. A compound according to claim 4, wherein mis
 3. 6. A compound according to claim 5, wherein R₃, R₄, and R₅ are allhydrogen.
 7. 2A,2B-Dihomo-4,4,5,5-tetradehydro-11-deoxy-PGE₁, methylester, a compound according to claim
 6. 8. A compound according to claim3, wherein g is one.
 9. A compound according to claim 8, wherein m is 3.10. A compound according to claim 9, wherein R₃ and R₄ are bothhydrogen.
 11. A compound according to claim 10, wherein R₅ is methyl.12. 4,4,5,5-Tetradehydro-15-methyl-11-deoxy-PGE₁, methyl ester, acompound according to claim
 11. 13.4,4,5,5-Tetradehydro-15-methyl-11-deoxy-PGE₁, a compound according toclaim
 11. 14. A compound according to claim 10, wherein R₅ is hydrogen.15. 4,4,5,5-Tetradehydro-11-deoxy-PGE₁, a compound according to claim14.
 16. 4,4,5,5-Tetradehydro-11-deoxy-PGE₁, methyl ester, a compoundaccording to claim
 14. 17. A compound according to claim 9, wherein atleast one of R₃ and R₄ is methyl.
 18. A compound according to claim 17,wherein R₃ and R₄ are both methyl.
 19. A compound according to claim 18,wherein R₅ is methyl. 20.4,4,5,5-Tetradehydro-15,16,16-trimethyl-11-deoxy-PGE₁, a compoundaccording to claim
 19. 21.4,4,5,5-Tetradehydro-15,16,16-trimethyl-11-deoxy-PGE₁, methyl ester, acompound according to claim
 19. 22. A compound according to claim 18,wherein R₅ is hydrogen. 23.4,4,5,5-Tetradehydro-16,16-dimethyl-11-deoxy-PGE₁, a compound accordingto claim
 22. 24. 4,4,5,5-Tetradehydro-16,16-dimethyl-11-deoxy-PGE₁,methyl ester, a compound according to claim
 22. 25. A compound accordingto claim 9, wherein at least one of R₃ and R₄ is fluoro.
 26. A compoundaccording to claim 25, wherein R₃ and R₄ are both fluoro.
 27. A compoundaccording to claim 26, wherein R₅ is methyl. 28.4,4,5,5-Tetradehydro-15-methyl-16,16-difluoro-11-deoxy-PGE₁, a compoundaccording to claim
 27. 29.4,4,5,5-Tetradehydro-15-methyl-16,16-difluoro-11-deoxy-PGE₁, methylester, a compound according to claim
 27. 30. A compound according toclaim 26, wherein R₅ is hydrogen. 31.4,4,5,5-Tetradehydro-16,16-difluoro-11-deoxy-PGE₁, a compound accordingto claim
 27. 32. 4,4,5,5-Tetradehydro-16,16-difluoro-11-deoxy-PGE₁,methyl ester, a compound according to claim 30.